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SML2282

Sigma-Aldrich

Everolimus

≥95% (HPLC), powder, P-glycoprotein substrate

Synonym(s):

Everolimus, 40-O-(2-Hydroxyethyl)rapamycin, 42-O-(2-Hydroxyethyl)-rapamycin, RAD 001, RAD001, SDZ-RAD, 42-O-(2-Hydroxyethyl)rapamycin

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About This Item

Empirical Formula (Hill Notation):
C53H83NO14
CAS Number:
159351-69-6
Molecular Weight:
958.22
MDL number:
MFCD00929329
UNSPSC Code:
12352200
NACRES:
NA.77

product name

Everolimus, ≥95% (HPLC)

Assay

≥95% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

shipped in

wet ice

storage temp.

−20°C

SMILES string

O=C(C([C@@]1(O)[C@H](C)CC[C@](C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C2=O)([H])O1)=O)N3[C@H](C(O[C@@]([C@@H](C[C@@]4([H])C[C@@H](OC)[C@H](OCCO)CC4)C)([H])CC([C@H](C)/C=C(C)/[C@@H](O)[C@H]2OC)=O)=O)CCCC3

InChI

1S/C53H83NO14/c1-32-16-12-11-13-17-33(2)44(63-8)30-40-21-19-38(7)53(62,68-40)50(59)51(60)54-23-15-14-18-41(54)52(61)67-45(35(4)28-39-20-22-43(66-25-24-55)46(29-39)64-9)31-42(56)34(3)27-37(6)48(58)49(65-10)47(57)36(5)26-32/h11-13,16-17,27,32,34-36,38-41,43-46,48-49,55,58,62H,14-15,18-26,28-31H2,1-10H3/b13-11+,16-12+,33-17+,37-27+/t32-,34-,35-,36-,38-,39+,40+,41+,43-,44+,45+,46-,48-,49+,53-/m1/s1

InChI key

HKVAMNSJSFKALM-GKUWKFKPSA-N

Gene Information

human ... FKBP1A(2280)

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Application

Everolimus has been used as an mechanistic target of rapamycin complex 1 (mTORC1) inhibitor to study its effect on MCF7 and MDA-MB-231 cell lines.

Biochem/physiol Actions

Everolimus, a substrate for P-glycoprotein (P-gp) can be used to treat advanced neuroendocrine tumors (NETs).
Everolimus, the 40-O-(2-hydroxyethyl) derivative of rapamycin (sirolimus), is a potent and selective inhibitor of mechanistic target of rapamycin (mTOR). Everolimus is selective for the mTORC1 protein complex. Everolimus exhibit potent immunosuppressive and anticancer activities.

Pictograms

Health hazardEnvironment
GHS08,GHS09

Signal Word

Warning

Hazard Statements

H351,H361fd,H373,H410

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - Carc. 2 - Repr. 2 - STOT RE 2

Target Organs

Kidney,Testes

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Chemical modification of rapamycin: the discovery of SDZ RAD.
R Sedrani et al.
Transplantation proceedings, 30(5), 2192-2194 (1998-09-02)
Everolimus in the treatment of neuroendocrine tumors: efficacy, side-effects, resistance, and factors affecting its place in the treatment sequence
Lee L, et al.
Expert Opinion on Pharmacotherapy, 19(8), 909-928 (2018)
Heidi A Lane et al.
Clinical cancer research : an official journal of the American Association for Cancer Research, 15(5), 1612-1622 (2009-02-19)
Comparison of the antiangiogenic/vascular properties of the oral mammalian target of rapamycin (mTOR) inhibitor RAD001 (everolimus) and the vascular endothelial growth factor receptor (VEGFR) inhibitor vatalanib (PTK/ZK). Antiproliferative activity against various tumor histotypes and downstream effects on the mTOR pathway
O-GlcNAc Transferase Inhibition Differentially Affects Breast Cancer Subtypes
Barkovskaya A, et al.
Scientific Reports, 9(1), 5670-5670 (2019)
Peter J Mullen et al.
Nature communications, 12(1), 1876-1876 (2021-03-27)
Viruses hijack host cell metabolism to acquire the building blocks required for replication. Understanding how SARS-CoV-2 alters host cell metabolism may lead to potential treatments for COVID-19. Here we profile metabolic changes conferred by SARS-CoV-2 infection in kidney epithelial cells
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